We propose to incorporate the indole moiety into 4-oxo-3- quinolinecarboxylic acids, a new class of potent antimicrobial agents also called "4-quinolones". Indoles having amine groups substituted in all possible ring positions will be synthesized and utilized as precursors of the potential antimicrobials. Condensation of these aminoindoles with beta-dicarbonyl adducts will provide acrylates which may be cyclized to the final 4-quinolone structure. Antimicrobial susceptibility testing will take place under the auspices of sub-project 2 (Dr. Chopra). We will also attempt to prepare Melatonin analogs with structural modifications as suggested by National Cancer Institute (NCI) researchers based upon the results of current testing for cell mitosis inhibition. These new compounds will also be submitted to NCI for testing as cell mitosis inhibitors. We also hope to evaluate the scope of the reaction of indoles with sodium bisulfite due to its potential significance to indole and medicinal chemistry. To accomplish this work, we intend involving undergraduate students in all aspects of the synthesis and characterization of these chemical compounds which will utilize at least 12 different types of chemical reactions some of which may be first-time applications in a specific area. The project allows room for expansion and/or more detailed examination of any particular facet of the research which may prove to warrant such.